A novel approach towards cis- and trans-fused pyranopyrans based on ring-closing metathesis reaction of carbohydrate derivatives

A novel synthesis of both cis-and trans-fused pyranopyran systems, based on ring-closing metathesis of glycal derived dienes, is described. Isomerisation of the resulting allylic double bond provides a new cyclic enol ether, thus opening the way to an iterative synthesis of cis-(trans-)fused cyclic...

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Bibliographic Details
Published inSynlett no. 11; pp. 1263 - 1265
Main Authors Leeuwenburgh, MA, Overkleeft, HS, vanderMarel, GA, vanBoom, JH
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ETHERS
REAGENTS
fused oxacycles
OLEFIN METATHESIS
glycals
ring-closing metathesis
BREVETOXIN-B
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Summary:A novel synthesis of both cis-and trans-fused pyranopyran systems, based on ring-closing metathesis of glycal derived dienes, is described. Isomerisation of the resulting allylic double bond provides a new cyclic enol ether, thus opening the way to an iterative synthesis of cis-(trans-)fused cyclic polyethers.
ISSN:0936-5214
DOI:10.1055/s-1997-1009